#------------------------------------------------------------------------------ #$Date: 2019-09-19 12:31:39 +0300 (Thu, 19 Sep 2019) $ #$Revision: 218546 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229904.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7229904 loop_ _publ_author_name 'Amombo Noa, Francoise M.' 'Mehlana, Gift' _publ_section_title ; Co-crystals and Salts of Vanillic Acid and Vanillin with Amines ; _journal_coden_ASTM CRECF4 _journal_issue 7 _journal_name_full CrystEngComm _journal_page_first 896 _journal_page_last 905 _journal_paper_doi 10.1039/c7ce02022h _journal_volume 20 _journal_year 2018 _chemical_formula_sum 'C22 H24 N6 O7' _chemical_formula_weight 484.47 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2017-12-07 deposited with the CCDC. 2018-01-08 downloaded from the CCDC. ; _cell_angle_alpha 70.022(3) _cell_angle_beta 78.358(3) _cell_angle_gamma 86.692(3) _cell_formula_units_Z 2 _cell_length_a 9.8016(14) _cell_length_b 10.7859(15) _cell_length_c 11.3248(16) _cell_measurement_reflns_used 12503 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.279 _cell_measurement_theta_min 1.950 _cell_volume 1102.0(3) _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXS-2017 (Sheldrick, 2017)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXS-2017 (Sheldrick, 2017)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_device_type 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_unetI/netI 0.0476 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.972 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 12503 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.972 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.279 _diffrn_reflns_theta_min 1.950 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour 'light brown' _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 508 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_transmission_factor_max 0.970 _exptl_transmission_factor_min 0.966 _refine_diff_density_max 0.582 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 336 _refine_ls_number_reflns 4823 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0540 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.3315P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1374 _refine_ls_wR_factor_ref 0.1519 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3560 _reflns_number_total 4823 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02022h2.cif _cod_data_source_block vacafnam _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas Updated bibliographic information. Antanas Vaitkus, 2019-09-19 ; _cod_database_code 7229904 _shelx_shelxl_version_number 2017/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _exptl_absorpt_special_details 'Absorption corrections were made using the program SADABS (Sheldrick, 1996)' _shelx_res_file ; TITL vacafnam in P-1 I:\VAANDV~1\VA_CAF~1\vacafnam.res created by SHELXL-2017/1 at 10:55:37 on 07-Dec-2017 CELL 0.71073 9.8016 10.7859 11.3248 70.022 78.358 86.692 ZERR 2.0000 0.0014 0.0015 0.0016 0.003 0.003 0.003 LATT 1 SFAC C H N O UNIT 44 48 12 14 CONF BOND EQIV $1 1-X,1-Y,1-Z EQIV $2 -X,1-Y,1-Z EQIV $3 X-1,Y,1+Z EQIV $4 -X,-Y,2-Z EQIV $5 1+X,Y,Z-1 HTAB C6 O5_$1 HTAB C16 O3_$2 HTAB C18 O5 HTAB C18 O3 HTAB C21 N1_$1 HTAB N2 O1_$3 HTAB N2 O7_$4 HTAB O2 O5_$5 HTAB O4 N5 ACTA FMAP 2 1 53 GRID PLAN 10 0 0 HTAB 2.0 MERG 2 TEMP -100 L.S. 20 WGHT 0.077600 0.331500 FVAR 0.23731 O3 4 0.461402 0.301507 0.419205 11.00000 0.02973 0.02285 = 0.03905 -0.00501 0.00768 -0.00364 O4 4 0.506520 0.563887 0.302540 11.00000 0.03211 0.02468 = 0.04457 -0.00871 0.01092 0.00169 O1 4 0.889261 0.096451 0.206048 11.00000 0.03048 0.02548 = 0.04777 -0.01064 0.00182 0.00024 O2 4 1.006351 0.277385 0.067851 11.00000 0.03496 0.02980 = 0.04299 -0.00952 0.01103 0.00024 C7 1 0.811443 0.443909 0.136186 11.00000 0.02420 0.02957 = 0.02475 -0.00674 0.00011 -0.00220 AFIX 43 H7 2 0.890147 0.479492 0.070572 11.00000 -1.20000 AFIX 0 C3 1 0.678276 0.256419 0.290380 11.00000 0.02832 0.02295 = 0.02913 -0.00878 -0.00552 -0.00063 AFIX 43 H3 2 0.666347 0.163621 0.330114 11.00000 -1.20000 AFIX 0 C6 1 0.713029 0.527810 0.172798 11.00000 0.03017 0.02337 = 0.02891 -0.00485 -0.00251 -0.00085 AFIX 43 H6 2 0.724581 0.620559 0.132311 11.00000 -1.20000 AFIX 0 C2 1 0.796076 0.308290 0.194528 11.00000 0.02650 0.02599 = 0.02593 -0.00934 -0.00461 -0.00030 C1 1 0.899766 0.216496 0.158081 11.00000 0.02494 0.03041 = 0.03049 -0.01122 -0.00364 0.00085 C4 1 0.579951 0.339972 0.326879 11.00000 0.02279 0.02576 = 0.02757 -0.00705 -0.00081 -0.00271 C8 1 0.436290 0.163146 0.480166 11.00000 0.03652 0.02376 = 0.04048 -0.00315 0.00700 -0.00522 AFIX 137 H8A 2 0.433957 0.122465 0.415323 11.00000 -1.50000 H8B 2 0.346724 0.148011 0.540300 11.00000 -1.50000 H8C 2 0.510934 0.123890 0.526762 11.00000 -1.50000 AFIX 0 C5 1 0.597972 0.477166 0.268066 11.00000 0.02752 0.02389 = 0.02926 -0.00911 -0.00296 0.00092 O5 4 0.193723 0.140626 0.972266 11.00000 0.02983 0.02063 = 0.04371 -0.00328 0.00652 -0.00066 O6 4 -0.116236 0.786727 0.637289 11.00000 0.03949 0.02369 = 0.04625 -0.00829 0.00094 0.00041 O7 4 -0.092879 0.337244 0.791593 11.00000 0.03492 0.02367 = 0.04619 0.00151 -0.00217 -0.00641 N6 3 0.162936 0.777920 0.458265 11.00000 0.02927 0.02224 = 0.02673 -0.00547 0.00145 -0.00190 N4 3 0.086353 0.444272 0.635463 11.00000 0.02951 0.02064 = 0.03210 -0.00614 -0.00492 -0.00155 N3 3 -0.101919 0.561042 0.713276 11.00000 0.02517 0.02189 = 0.02948 -0.00416 0.00028 -0.00370 C9 1 0.206041 0.018853 1.013602 11.00000 0.02307 0.02544 = 0.02896 -0.00774 -0.00242 -0.00037 N5 3 0.262877 0.584092 0.464724 11.00000 0.03001 0.03142 = 0.03211 -0.00944 0.00044 -0.00165 C17 1 -0.038684 0.441173 0.717732 11.00000 0.02735 0.02303 = 0.03141 -0.00438 -0.00659 -0.00425 C19 1 0.142256 0.564682 0.552152 11.00000 0.02701 0.02958 = 0.02521 -0.00519 -0.00414 -0.00800 N2 3 0.109993 -0.058026 1.106188 11.00000 0.02900 0.02274 = 0.03881 -0.00456 0.00542 -0.00144 C15 1 -0.050840 0.687933 0.632693 11.00000 0.03164 0.02119 = 0.02796 -0.00373 -0.00535 -0.00529 N1 3 0.535509 -0.008249 0.792162 11.00000 0.03331 0.03790 = 0.03545 -0.00831 0.00366 0.00349 C16 1 -0.234402 0.556800 0.801494 11.00000 0.03056 0.03740 = 0.03871 -0.00559 0.00681 -0.00342 AFIX 137 H16A 2 -0.221437 0.594142 0.866195 11.00000 -1.50000 H16B 2 -0.266980 0.465105 0.843701 11.00000 -1.50000 H16C 2 -0.303574 0.608311 0.753705 11.00000 -1.50000 AFIX 0 C10 1 0.331284 -0.044054 0.959003 11.00000 0.02155 0.02566 = 0.02904 -0.00981 -0.00359 -0.00074 C14 1 0.418865 0.034329 0.849042 11.00000 0.03127 0.02720 = 0.03347 -0.00470 -0.00007 0.00136 AFIX 43 H14 2 0.394010 0.123744 0.812198 11.00000 -1.20000 AFIX 0 C18 1 0.161352 0.321557 0.643596 11.00000 0.03668 0.03083 = 0.04599 -0.01419 -0.00829 0.00589 AFIX 137 H18A 2 0.107957 0.264458 0.617798 11.00000 -1.50000 H18B 2 0.173637 0.276506 0.731896 11.00000 -1.50000 H18C 2 0.252794 0.341354 0.586550 11.00000 -1.50000 AFIX 0 C13 1 0.568935 -0.134487 0.847215 11.00000 0.02896 0.03582 = 0.03836 -0.01507 -0.00215 0.00431 AFIX 43 H13 2 0.652309 -0.166743 0.809113 11.00000 -1.20000 AFIX 0 C22 1 0.077673 0.679969 0.551160 11.00000 0.02808 0.02460 = 0.02522 -0.00429 -0.00329 -0.00589 C12 1 0.489385 -0.219413 0.955384 11.00000 0.03273 0.02624 = 0.04339 -0.00929 -0.00363 0.00343 AFIX 43 H12 2 0.516875 -0.308279 0.990519 11.00000 -1.20000 AFIX 0 C11 1 0.368610 -0.173540 1.012380 11.00000 0.02754 0.02737 = 0.03492 -0.00550 -0.00003 -0.00176 AFIX 43 H11 2 0.311820 -0.230496 1.087526 11.00000 -1.20000 AFIX 0 C20 1 0.271132 0.715914 0.409731 11.00000 0.03113 0.03132 = 0.03288 -0.01066 0.00329 -0.00170 AFIX 43 H20 2 0.345675 0.760700 0.343423 11.00000 -1.20000 AFIX 0 C21 1 0.144873 0.920630 0.424016 11.00000 0.04137 0.02487 = 0.04195 -0.00304 0.00531 -0.00244 AFIX 137 H21A 2 0.223264 0.966001 0.356971 11.00000 -1.50000 H21B 2 0.141524 0.946166 0.499697 11.00000 -1.50000 H21C 2 0.057729 0.945339 0.392435 11.00000 -1.50000 AFIX 0 H2B 2 0.039576 -0.013723 1.143491 11.00000 0.06770 H2A 2 0.116178 -0.148054 1.129362 11.00000 0.05730 H2 2 1.066992 0.216489 0.041701 11.00000 0.07961 H5 2 0.440812 0.525467 0.365963 11.00000 0.07113 HKLF 4 REM vacafnam in P-1 REM R1 = 0.0540 for 3560 Fo > 4sig(Fo) and 0.0768 for all 4823 data REM 336 parameters refined using 0 restraints END WGHT 0.0776 0.3315 REM Instructions for potential hydrogen bonds HTAB C6 O5_$1 HTAB C16 O3_$2 HTAB C18 O5 HTAB C18 O3 HTAB C21 N1_$1 HTAB N2 O1_$3 HTAB N2 O7_$4 HTAB O2 O5_$5 HTAB O4 N5 REM Highest difference peak 0.582, deepest hole -0.284, 1-sigma level 0.056 Q1 1 0.2712 0.4767 0.4968 11.00000 0.05 0.58 Q2 1 0.0629 0.8484 0.5043 11.00000 0.05 0.43 Q3 1 0.1240 0.2404 0.7053 11.00000 0.05 0.31 Q4 1 0.2842 0.8249 0.3590 11.00000 0.05 0.26 Q5 1 -0.3063 0.4955 0.7719 11.00000 0.05 0.26 Q6 1 0.2642 -0.0203 0.9680 11.00000 0.05 0.24 Q7 1 -0.2715 0.6401 0.8206 11.00000 0.05 0.24 Q8 1 -0.2215 0.4829 0.9017 11.00000 0.05 0.24 Q9 1 0.1667 0.3057 0.5631 11.00000 0.05 0.23 Q10 1 0.1240 0.6220 0.5928 11.00000 0.05 0.22 ; _shelx_res_checksum 94543 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp O3 O 0.46140(15) 0.30151(14) 0.41921(14) 0.0339(4) Uani 1 1 d . . O4 O 0.50652(17) 0.56389(15) 0.30254(16) 0.0374(4) Uani 1 1 d . . O1 O 0.88926(15) 0.09645(14) 0.20605(15) 0.0364(4) Uani 1 1 d . . O2 O 1.00635(17) 0.27738(16) 0.06785(16) 0.0394(4) Uani 1 1 d . . C7 C 0.8114(2) 0.4439(2) 0.13619(19) 0.0274(4) Uani 1 1 d . . H7 H 0.890147 0.479492 0.070572 0.033 Uiso 1 1 calc R U C3 C 0.6783(2) 0.2564(2) 0.29038(19) 0.0268(4) Uani 1 1 d . . H3 H 0.666347 0.163621 0.330114 0.032 Uiso 1 1 calc R U C6 C 0.7130(2) 0.5278(2) 0.17280(19) 0.0290(5) Uani 1 1 d . . H6 H 0.724581 0.620559 0.132311 0.035 Uiso 1 1 calc R U C2 C 0.7961(2) 0.30829(19) 0.19453(19) 0.0260(4) Uani 1 1 d . . C1 C 0.8998(2) 0.2165(2) 0.1581(2) 0.0286(5) Uani 1 1 d . . C4 C 0.5800(2) 0.33997(19) 0.32688(19) 0.0264(4) Uani 1 1 d . . C8 C 0.4363(2) 0.1631(2) 0.4802(2) 0.0375(5) Uani 1 1 d . . H8A H 0.433957 0.122465 0.415323 0.056 Uiso 1 1 calc R U H8B H 0.346724 0.148011 0.540300 0.056 Uiso 1 1 calc R U H8C H 0.510934 0.123890 0.526762 0.056 Uiso 1 1 calc R U C5 C 0.5980(2) 0.4772(2) 0.26807(19) 0.0273(4) Uani 1 1 d . . O5 O 0.19372(15) 0.14063(14) 0.97227(15) 0.0354(4) Uani 1 1 d . . O6 O -0.11624(16) 0.78673(14) 0.63729(16) 0.0388(4) Uani 1 1 d . . O7 O -0.09288(16) 0.33724(14) 0.79159(15) 0.0390(4) Uani 1 1 d . . N6 N 0.16294(18) 0.77792(16) 0.45826(16) 0.0277(4) Uani 1 1 d . . N4 N 0.08635(18) 0.44427(16) 0.63546(16) 0.0282(4) Uani 1 1 d . . N3 N -0.10192(17) 0.56104(16) 0.71328(16) 0.0274(4) Uani 1 1 d . . C9 C 0.2060(2) 0.01885(19) 1.01360(19) 0.0266(4) Uani 1 1 d . . N5 N 0.26288(19) 0.58409(18) 0.46472(17) 0.0324(4) Uani 1 1 d . . C17 C -0.0387(2) 0.44117(19) 0.7177(2) 0.0282(4) Uani 1 1 d . . C19 C 0.1423(2) 0.5647(2) 0.55215(19) 0.0281(4) Uani 1 1 d . . N2 N 0.10999(19) -0.05803(19) 1.10619(18) 0.0334(4) Uani 1 1 d . . C15 C -0.0508(2) 0.6879(2) 0.63269(19) 0.0280(4) Uani 1 1 d . . N1 N 0.5355(2) -0.00825(19) 0.79216(18) 0.0383(5) Uani 1 1 d . . C16 C -0.2344(2) 0.5568(2) 0.8015(2) 0.0393(5) Uani 1 1 d . . H16A H -0.221437 0.594142 0.866195 0.059 Uiso 1 1 calc R U H16B H -0.266980 0.465105 0.843701 0.059 Uiso 1 1 calc R U H16C H -0.303574 0.608311 0.753705 0.059 Uiso 1 1 calc R U C10 C 0.3313(2) -0.04405(19) 0.95900(19) 0.0254(4) Uani 1 1 d . . C14 C 0.4189(2) 0.0343(2) 0.8490(2) 0.0331(5) Uani 1 1 d . . H14 H 0.394010 0.123744 0.812198 0.040 Uiso 1 1 calc R U C18 C 0.1614(2) 0.3216(2) 0.6436(2) 0.0377(5) Uani 1 1 d . . H18A H 0.107957 0.264458 0.617798 0.057 Uiso 1 1 calc R U H18B H 0.173637 0.276506 0.731896 0.057 Uiso 1 1 calc R U H18C H 0.252794 0.341354 0.586550 0.057 Uiso 1 1 calc R U C13 C 0.5689(2) -0.1345(2) 0.8472(2) 0.0345(5) Uani 1 1 d . . H13 H 0.652309 -0.166743 0.809113 0.041 Uiso 1 1 calc R U C22 C 0.0777(2) 0.67997(19) 0.55116(19) 0.0271(4) Uani 1 1 d . . C12 C 0.4894(2) -0.2194(2) 0.9554(2) 0.0355(5) Uani 1 1 d . . H12 H 0.516875 -0.308279 0.990519 0.043 Uiso 1 1 calc R U C11 C 0.3686(2) -0.1735(2) 1.0124(2) 0.0321(5) Uani 1 1 d . . H11 H 0.311820 -0.230496 1.087526 0.038 Uiso 1 1 calc R U C20 C 0.2711(2) 0.7159(2) 0.4097(2) 0.0331(5) Uani 1 1 d . . H20 H 0.345675 0.760700 0.343423 0.040 Uiso 1 1 calc R U C21 C 0.1449(3) 0.9206(2) 0.4240(2) 0.0401(6) Uani 1 1 d . . H21A H 0.223264 0.966001 0.356971 0.060 Uiso 1 1 calc R U H21B H 0.141524 0.946166 0.499697 0.060 Uiso 1 1 calc R U H21C H 0.057729 0.945339 0.392435 0.060 Uiso 1 1 calc R U H2B H 0.040(3) -0.014(3) 1.143(3) 0.068(9) Uiso 1 1 d . . H2A H 0.116(3) -0.148(3) 1.129(3) 0.057(8) Uiso 1 1 d . . H2 H 1.067(4) 0.216(3) 0.042(3) 0.080(10) Uiso 1 1 d . . H5 H 0.441(3) 0.525(3) 0.366(3) 0.071(10) Uiso 1 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0297(8) 0.0229(8) 0.0391(9) -0.0050(6) 0.0077(6) -0.0036(6) O4 0.0321(8) 0.0247(8) 0.0446(9) -0.0087(7) 0.0109(7) 0.0017(6) O1 0.0305(8) 0.0255(8) 0.0478(9) -0.0106(7) 0.0018(7) 0.0002(6) O2 0.0350(9) 0.0298(8) 0.0430(9) -0.0095(7) 0.0110(7) 0.0002(7) C7 0.0242(10) 0.0296(11) 0.0247(10) -0.0067(8) 0.0001(8) -0.0022(8) C3 0.0283(11) 0.0229(10) 0.0291(10) -0.0088(8) -0.0055(8) -0.0006(8) C6 0.0302(11) 0.0234(10) 0.0289(11) -0.0049(8) -0.0025(8) -0.0009(8) C2 0.0265(10) 0.0260(10) 0.0259(10) -0.0093(8) -0.0046(8) -0.0003(8) C1 0.0249(10) 0.0304(12) 0.0305(11) -0.0112(9) -0.0036(8) 0.0009(8) C4 0.0228(10) 0.0258(10) 0.0276(10) -0.0070(8) -0.0008(8) -0.0027(8) C8 0.0365(12) 0.0238(11) 0.0405(13) -0.0032(9) 0.0070(10) -0.0052(9) C5 0.0275(11) 0.0239(10) 0.0293(10) -0.0091(8) -0.0030(8) 0.0009(8) O5 0.0298(8) 0.0206(8) 0.0437(9) -0.0033(6) 0.0065(6) -0.0007(6) O6 0.0395(9) 0.0237(8) 0.0462(10) -0.0083(7) 0.0009(7) 0.0004(7) O7 0.0349(9) 0.0237(8) 0.0462(9) 0.0015(7) -0.0022(7) -0.0064(6) N6 0.0293(9) 0.0222(9) 0.0267(9) -0.0055(7) 0.0015(7) -0.0019(7) N4 0.0295(9) 0.0206(9) 0.0321(9) -0.0061(7) -0.0049(7) -0.0015(7) N3 0.0252(9) 0.0219(9) 0.0295(9) -0.0042(7) 0.0003(7) -0.0037(7) C9 0.0231(10) 0.0254(11) 0.0290(10) -0.0077(8) -0.0024(8) -0.0004(8) N5 0.0300(10) 0.0314(10) 0.0321(10) -0.0094(8) 0.0004(7) -0.0017(7) C17 0.0274(11) 0.0230(10) 0.0314(11) -0.0044(8) -0.0066(8) -0.0042(8) C19 0.0270(11) 0.0296(11) 0.0252(10) -0.0052(8) -0.0041(8) -0.0080(8) N2 0.0290(10) 0.0227(10) 0.0388(11) -0.0046(8) 0.0054(8) -0.0014(8) C15 0.0316(11) 0.0212(10) 0.0280(10) -0.0037(8) -0.0054(8) -0.0053(8) N1 0.0333(10) 0.0379(11) 0.0354(10) -0.0083(8) 0.0037(8) 0.0035(8) C16 0.0306(12) 0.0374(13) 0.0387(13) -0.0056(10) 0.0068(9) -0.0034(10) C10 0.0215(10) 0.0257(10) 0.0290(10) -0.0098(8) -0.0036(8) -0.0007(8) C14 0.0313(11) 0.0272(11) 0.0335(11) -0.0047(9) -0.0001(9) 0.0014(9) C18 0.0367(12) 0.0308(12) 0.0460(13) -0.0142(10) -0.0083(10) 0.0059(10) C13 0.0290(11) 0.0358(12) 0.0384(12) -0.0151(10) -0.0021(9) 0.0043(9) C22 0.0281(11) 0.0246(10) 0.0252(10) -0.0043(8) -0.0033(8) -0.0059(8) C12 0.0327(12) 0.0262(11) 0.0434(13) -0.0093(9) -0.0036(10) 0.0034(9) C11 0.0275(11) 0.0274(11) 0.0349(11) -0.0055(9) 0.0000(9) -0.0018(8) C20 0.0311(11) 0.0313(12) 0.0329(11) -0.0107(9) 0.0033(9) -0.0017(9) C21 0.0414(13) 0.0249(11) 0.0420(13) -0.0030(10) 0.0053(10) -0.0024(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4 O3 C8 116.98(16) C6 C7 C2 120.53(19) C4 C3 C2 120.18(18) C5 C6 C7 120.26(19) C7 C2 C3 119.35(18) C7 C2 C1 121.72(18) C3 C2 C1 118.93(18) O1 C1 O2 123.12(19) O1 C1 C2 123.74(19) O2 C1 C2 113.14(18) O3 C4 C3 125.63(18) O3 C4 C5 114.59(17) C3 C4 C5 119.78(18) O4 C5 C6 117.84(18) O4 C5 C4 122.25(18) C6 C5 C4 119.90(18) C20 N6 C22 106.08(17) C20 N6 C21 126.39(18) C22 N6 C21 127.44(18) C17 N4 C19 119.12(18) C17 N4 C18 119.37(17) C19 N4 C18 121.39(19) C17 N3 C15 126.75(17) C17 N3 C16 117.23(17) C15 N3 C16 116.02(17) O5 C9 N2 121.56(19) O5 C9 C10 119.77(18) N2 C9 C10 118.66(18) C20 N5 C19 103.27(18) O7 C17 N4 121.43(19) O7 C17 N3 120.95(19) N4 C17 N3 117.62(17) N5 C19 C22 112.24(18) N5 C19 N4 126.2(2) C22 C19 N4 121.54(19) O6 C15 N3 120.83(19) O6 C15 C22 128.08(19) N3 C15 C22 111.08(18) C14 N1 C13 116.66(19) C11 C10 C14 117.60(19) C11 C10 C9 124.53(18) C14 C10 C9 117.84(18) N1 C14 C10 124.1(2) N1 C13 C12 123.6(2) C19 C22 N6 105.41(18) C19 C22 C15 123.88(18) N6 C22 C15 130.71(19) C13 C12 C11 118.8(2) C10 C11 C12 119.3(2) N5 C20 N6 113.01(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O3 C4 1.373(2) O3 C8 1.426(2) O4 C5 1.357(2) O1 C1 1.222(2) O2 C1 1.325(3) C7 C6 1.384(3) C7 C2 1.387(3) C3 C4 1.380(3) C3 C2 1.406(3) C6 C5 1.383(3) C2 C1 1.476(3) C4 C5 1.405(3) O5 C9 1.242(2) O6 C15 1.223(3) O7 C17 1.219(2) N6 C20 1.345(3) N6 C22 1.382(3) N6 C21 1.463(3) N4 C17 1.376(3) N4 C19 1.383(3) N4 C18 1.460(3) N3 C17 1.391(3) N3 C15 1.413(2) N3 C16 1.462(3) C9 N2 1.331(3) C9 C10 1.495(3) N5 C20 1.343(3) N5 C19 1.355(3) C19 C22 1.360(3) C15 C22 1.421(3) N1 C14 1.333(3) N1 C13 1.342(3) C10 C11 1.380(3) C10 C14 1.391(3) C13 C12 1.370(3) C12 C11 1.380(3) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C6 H6 O5 0.95 2.54 3.476(3) 168.5 2_666 yes C16 H16C O3 0.98 2.63 3.574(3) 161.6 2_566 yes C18 H18B O5 0.98 2.66 3.634(3) 175.7 . yes C18 H18C O3 0.98 2.62 3.527(3) 154.5 . yes C21 H21A N1 0.98 2.58 3.517(3) 160.8 2_666 yes N2 H2B O1 0.93(3) 2.01(3) 2.936(2) 174(3) 1_456 yes N2 H2A O7 0.92(3) 1.93(3) 2.835(2) 167(3) 2_557 yes O2 H2 O5 0.94(4) 1.66(4) 2.588(2) 167(3) 1_654 yes O4 H5 N5 0.86(3) 2.06(3) 2.751(2) 136(3) . yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C2 C7 C6 C5 -0.1(3) C6 C7 C2 C3 0.8(3) C6 C7 C2 C1 -179.59(19) C4 C3 C2 C7 -0.8(3) C4 C3 C2 C1 179.66(18) C7 C2 C1 O1 -179.11(19) C3 C2 C1 O1 0.5(3) C7 C2 C1 O2 1.1(3) C3 C2 C1 O2 -179.37(18) C8 O3 C4 C3 -1.7(3) C8 O3 C4 C5 178.68(18) C2 C3 C4 O3 -179.71(18) C2 C3 C4 C5 -0.1(3) C7 C6 C5 O4 178.35(19) C7 C6 C5 C4 -0.8(3) O3 C4 C5 O4 1.4(3) C3 C4 C5 O4 -178.23(19) O3 C4 C5 C6 -179.47(18) C3 C4 C5 C6 0.9(3) C19 N4 C17 O7 178.97(18) C18 N4 C17 O7 -4.9(3) C19 N4 C17 N3 -0.6(3) C18 N4 C17 N3 175.45(18) C15 N3 C17 O7 -179.95(19) C16 N3 C17 O7 0.7(3) C15 N3 C17 N4 -0.3(3) C16 N3 C17 N4 -179.70(18) C20 N5 C19 C22 0.3(2) C20 N5 C19 N4 -179.52(19) C17 N4 C19 N5 -179.15(19) C18 N4 C19 N5 4.8(3) C17 N4 C19 C22 1.1(3) C18 N4 C19 C22 -174.94(19) C17 N3 C15 O6 179.9(2) C16 N3 C15 O6 -0.8(3) C17 N3 C15 C22 0.8(3) C16 N3 C15 C22 -179.81(18) O5 C9 C10 C11 167.5(2) N2 C9 C10 C11 -12.5(3) O5 C9 C10 C14 -10.4(3) N2 C9 C10 C14 169.7(2) C13 N1 C14 C10 -0.8(3) C11 C10 C14 N1 0.4(3) C9 C10 C14 N1 178.4(2) C14 N1 C13 C12 0.9(3) N5 C19 C22 N6 -0.4(2) N4 C19 C22 N6 179.41(17) N5 C19 C22 C15 179.66(19) N4 C19 C22 C15 -0.5(3) C20 N6 C22 C19 0.4(2) C21 N6 C22 C19 -176.3(2) C20 N6 C22 C15 -179.7(2) C21 N6 C22 C15 3.6(4) O6 C15 C22 C19 -179.3(2) N3 C15 C22 C19 -0.4(3) O6 C15 C22 N6 0.8(4) N3 C15 C22 N6 179.70(19) N1 C13 C12 C11 -0.6(4) C14 C10 C11 C12 0.0(3) C9 C10 C11 C12 -177.9(2) C13 C12 C11 C10 0.1(3) C19 N5 C20 N6 0.0(2) C22 N6 C20 N5 -0.2(2) C21 N6 C20 N5 176.5(2)